1-Bromonaphthalene

1-Bromonaphthalene is an organic compound with the formula C10H7Br.

1-Bromonaphthalene
1-Bromonaphthalene
Names
Preferred IUPAC name
1-Bromonaphthalene
Other names
α-Bromonaphthalene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.001.787
EC Number
  • 201-965-2
MeSH C108222
UNII
  • InChI=1S/C10H7Br/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7H
    Key: DLKQHBOKULLWDQ-UHFFFAOYSA-N
  • InChI=1/C10H7Br/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7H
    Key: DLKQHBOKULLWDQ-UHFFFAOYAA
  • c1ccc2c(c1)cccc2Br
Properties
C10H7Br
Molar mass 207.07
Appearance colorless liquid
Density 1.48 g/mL
Melting point 1-2 ºC
Boiling point 132–135 °C at 12 mm; 145–148 °C at 20 mm
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

It is one of two isomeric bromonaphthalenes, the other being 2-bromonaphthalene. Under normal conditions, the substance is a colorless liquid.

Synthesis and reactions

It is prepared by treatment of naphthalene with bromine:[1]

C10H8 + Br2 → C10H7Br + HBr

The compound exhibits many reactions typical of aryl bromides. Bromide can be displaced by cyanide to give the nitrile. It forms a Grignard reagent[2] and organolithium compound. 1-Lithionaphthalene can be further lithiated to give 1,8-dilithionaphthalene, a precursor to peri-naphthalene compounds.

Applications

Because of its high refractive index, (1.656-1.659nD) [3] 1-bromonaphthalene is used as an embedding agent in microscopy and for determining the refraction of crystals.

The compound is also used as a precursor to various substituted derivatives of naphthalene.

See also

References
  1. H. T. Clarke and M. R. Brethen "α-Bromonaphthalene" Org. Synth. 1921, volume 1, 35. doi:10.15227/orgsyn.001.0035
  2. Henry Gilman, Nina B. St. John, and F. Schulze "α-Naphthoic Acid" Org. Synth. 1931, volume 11, 80. doi:10.15227/orgsyn.011.0080
  3. "1-Bromonaphthalene".
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